Normal secondary nonadecyl sulphates



Patented July 8,1947

NORMAL. ssconmuty NONADECYL SULPHATES Emil. E. Dreger, Summit, and John Ross Ramsey,

assignors to Colgate-Paimoiive-Peet Company, Jersey City, N. 1., a corporation of Delaware No Drawing. Original applieation luiy e, 1937,

Serial No. 152,852. Divided and this application May 26, 1943, Serial No. 488,558

6 Claims. 1 v This invention relates to new materials adapted to function as wetting agents, detergents or the like. More particularly, the invention relates to the utilization of short chain fatty acids, which are not ordinarily satisfactory for the preparation of detergents, wetting agents, and the like,

for the production of materials which will function efficiently for these purposes.

The fatty oils that are commonly used in the production of detergent materials almost invariably contain an appreciable percentage of fatty acid esters, the fatty acids of which contain less than 12 carbon atoms. The sodium salts of these fatty acids are of little or no value and, if they are left in the mixture along with the salts of the higher fatty acids, the result is simply a corresponding amount of inactive or ineflicient material in the final product. This fact has been recognized and in some instances these lower fatty acids have been removed to make the final product more eflective.

The removal of such fatty acids, however, reduces the quantity of the final detergent product that can be produced from a given amount of fatty oil and yields, as a by-product, considerable quantities of these lower fatty acids. For example,v about 21% of the fatty acids in coconut oil contains less than 12 carbon atoms, and about 13% of the acids in palm kernel oil also contains less than 12 carbon atoms.

According to the present process, these fatty acids, containing more than 1 and less than 12 carbon atoms and which are almost entirely of the straight chain or normal variety, are reacted in such a way as to form useful, efficient detergents, wetting agents, or the like. Preferably, the fatty acids that are used according to the present process are straight chain fatty acids and have at least 6 and not over 11 carbon atoms;

Briefly, the process of the present invention is accomplished by converting the fatty acids into ketones, usually straight chain ketones since the fatty acids used are generally straight chain fatty acids; thereafter hydrogenating the ketones to form secondary alcohols; and finally sulphating the alcohols to produce secondary alcohol sulphuric acid esters. The acid esters may then be neutralized with lime, ammonia, alkali metal hydroxides or carbonates before use. The process is further described and is claimed in our copending application Serial No. 152,852, filed July 9, 1937, now Patent No. 2,321,020, granted June 8,

Q carbinol sulphate salt respectively. The mixture of caprylic and capric acid gave a mixture of di n-nonyl carbinol sulphate salt, di n-heptyl carbinol sulphate salt and n-heptyl n-nonyl carbinol sulphate salt. The mixture of all three acids produced in addition to the others n-amyl nheptyl carbinol sulphate salt and n-amyl n-nonyl carbinol sulphate salt.

The relative wetting and foaming properties of solutions ofsome of the compounds are compared below, showing the outstanding and unusual efilciency of di n-heptyl carbinol sulphate sodium salt in these respects.

Foam, cc. Wetting Time Material &2}?

1% Water, 1.0% 0.25% 0.1%

tion 500 P. P. M.

Di-n-heptyl carbinol sulphate sodium salt GisHsiO SOQNE 600 1 2 1O n-Heptyl n-nonyl carbinol sulgiate sodium salt C11 :50 S0;Na 400 20 2 9 Di-n-nonyl carbinol sulhate sodium salt 819E390 SO3N8 275 10 9 50 Mixed sodium salts of carbinol sulphates from mixtures of Ca, 0|, Cm acids 350 60 2 17 1943, of which the present application is a divin-heptyl carbinol sulphate salt, and-di-n-nonyl beaker, the time required to wet the square of cloth dropped upon the surface of the solution can be readily measured with a stop watch. In most cases the cloth will sink to the bottom as soon as it is thoroughly wet.

Generally the secondary alcohol sulphates pre pared by the process should contain at least 11 carbon atoms to be satisfactory as emulsifying and deterging agents. is used to preparethe secondary alcohol it should contain at least 6 carbon atoms and, if a mixture of acids is used, the sum of the carbons in their chains should be at least equal to 12 carbon atoms. For example, n-butyric acid (4) and -n-caprylic acid (8) will yield along with other sulphates, n-propyl n-heptyl' carbinol sulphate salt which has 11 carbon atoms in the compound.

Although the preferred compounds are prepared from the straight chainfatty acids con- That is, if a single acid taming not less than 6 and not more than 11 carbon atoms, the process is adapted to the use of i any straight or branch chain aliphatic monocarboxylic acids other than formic acid, 1. e., acetic 4 The present invention is not to be'restricted to any specific proportions or manner of procedure beyond the limitation of the appended claims.

We claim:

acid and its higher homologues, whether derived 5 1. A normal secondary nonadecyl sulphate. from fatty oils or from any other source, such as 2. Di-n-nonyl carbinol sulphate. the oxidation of petroleum, alcohols and alde- 3. A normal secondary nonadecyl sulphate hydes, de-esterification of oils, fats and waxes salt. and by organic synthesis. 4. Di-n-nonyl carbinol sulphate salt.

Mixtures of lauric and n-butyric and of lauric 5. A normal secondary nonadecyl sulphate soand isobutyric acids were converted into ketones dium salt. and the pure n-propyi undecyl ketone and 150- 6. Di-n-nonyl carbinol sulphate sodium salt. propyl undecyl ketoneobtained by fractionation. EMI EL DRE These were reduced to the respective carbinols JOHN Ross, which were converted into acid sulphates and neutralized. REFERENCES CITED following comparison of the Wetting and The following references are of record in the foaming properties of these two isomeric comm of this patent: pounds discloses the marked superiority of the straight chain compound as a wetting agent. UNITED STATES PATENTS Number Name Date Foam m Wetting 2,027,896 Bertsch Jan. 14, 1936 Time 2,229,649 Guenther et a1 Jan 28, 1941 2,326,270 Werntz Aug. 10, 1943 2,103,133 McCall Feb. 15,1938 tion age 2,088,019 Wickert July 27, 1937 FOREIGN PATENTS Number Country Date $2.122 533 ?;i? "c.. I 343,872 Great Britain Feb. 3, 1931 i l iiaafiman-rm: 73 0 n phat? sodium salt CnHu THEE REFERENCES 0503M 2 22 Messer, Chem. News, vol. 138, pp. 292-3 

